US4239751A - Antibiotic substances - Google Patents

Antibiotic substances Download PDF

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US4239751A
US4239751A US06/030,492 US3049279A US4239751A US 4239751 A US4239751 A US 4239751A US 3049279 A US3049279 A US 3049279A US 4239751 A US4239751 A US 4239751A
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sub
butanol
water
positive
saturated
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US06/030,492
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Carolina Coronelli
Grazia Beretta
Maria R. Bardone
Francesco Parenti
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Gruppo Lepetit SpA
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Gruppo Lepetit SpA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/06—Fungi, e.g. yeasts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

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  • the new antibiotics mixture and the individual factors are obtained by fermentation of a strain belonging to the genus Actinoplanes named Actinoplanes teichomyceticus nov. sp. and identified with our internal code A/8327.
  • the strain has been deposited and made part of the stock culture collection of ATCC where it was assigned the number 31121.
  • Actinoplanes teichomyceticus nov. sp. ATCC 31121 is cultivated under aerobic conditions in an aqueous nutrient medium which is suitable for the growth of said organism.
  • the medium contains an assimilable source of carbon, an assimilable source of nitrogen and inorganic salts.
  • the antibiotic-producing strain is pre-cultured in a shake flask until substantial mycelial growth is present, then the culture is used to inoculate jar fermentors containing nutrient fermentative medium. Cultivation is continued, preferably at a temperature between about 25° C.
  • microbiological assays are carried out by the agar diffusion method to control the concentration of the antibiotic substance produced.
  • the fermentation broth is filtered in order to separate the mycelial cake.
  • the antibiotics mixture is isolated from the filtered fermentation broth by conventional procedures, such as, for example, by extraction with an organic solvent in which the antibiotic mixture is soluble and which is immiscible with the aqueous medium.
  • the extraction is carried out after adjustment of the pH of the fermentation broth to about 3.5.
  • Suitable organic solvents for the extraction are advantageously selected from halogenated C 1 -C 4 hydrocarbons and C 4 -C 6 alkanols.
  • the solvent is then separated from the fermentation broth by high-speed centrifugation, concentrated to about 1/10-1/20 of its original volume, cooled and allowed to stand until a precipitate forms which is recovered on filter.
  • This precipitate essentially consists of antibiotic 8327 factor A (hereinafter alternatively referred to as teichomycin), which is a mixture of teichomycin A 1 , teichomycin A 2 and teichomycin A 3 .
  • Antibiotic 8327 factors B and C essentially remain in the organic solution and are precipitated by addition of a large amount of an inert non-polar solvent such as, for example, a light petroleum.
  • Teichomycin A 1 , teichomycin A 2 and teichomycin A 3 are separated from each other by column chromatography while antibiotic 8327 factors B and C are separated from each other by means of counter current distribution techniques. Additional product may be recovered by extracting the mycelial cake with aqueous acetone. After distillation of the acetone, the aqueous phase is submitted to the same treatment described above for the filtered fermentation broth.
  • the strain Actinoplanes teichomyceticus nov. sp. ATCC 31121 was isolated from a soil sample collected at Nimodi Village, Indore (India). The strain grows well on various nutrient agars. In oatmeal agar, the colonies are approximately 5 to 6 mm in diameter, show regular contours and a central dome-like protuberance. An abundant sterile aerial mycelium is found on some media.
  • Sporangia are abundantly produced on most media and are mainly found on the dome of the colony. They are spherical to oval in shape, have regular contours and a diameter ranging from about 15 to about 25 m ⁇ . Sporangiospores are straight, about 15 m ⁇ long with a diameter of about 2 m ⁇ . The spores are highly motile and are spherical to oval with a diameter of about 1.5-2 m ⁇ .
  • Table I reports the cultural characteristics of Actinoplanes teichomyceticus nov. sp. ATCC 31121 cultivated on various standard media suggested by Shirling and Gottlieb (Int. J. Syst. Bacteriol., 16, 313-340, 1966) and other media recommended by Waksman (The Actinomycetes, Vol. II, The Williams and Wilkins Co., 1961). The cultural characteristics were determined after 6-14 days of incubation at 30° C.
  • Table II reports the utilization of carbon sources examined according to the method of Pridham and Gottling (Journal Bacteriol., 56, 197, 1948).
  • Table III reports the physiological characteristics of the strain.
  • the strain Actinoplanes teichomyceticus nov. sp. ATCC 31121 has been cultured concomitantly with: A. brasiliensis, A. missourensis, A. uthaensis, A. filippinensis, A. italicus, A. armeniacus, A. deccanensis ATCC 21983, A. garbadinensis ATCC 31049, and A. liguriae ATCC 31048. It could be clearly distinguished from all these species on the basis of morphological and pigmentation characteristics. In addition, it peptonizes litmus milk, an infrequent feature shared with the cherry-rose pigmented A. italicus.
  • the strain Actinoplanes teichomyceticus nov. sp. ATCC 31121 is aerobically pre-cultured in a nutrient medium until substantial mycelial growth is present, at a pH value ranging from about 6 to about 8.
  • a shake flask culture may have the following composition in g/l.
  • the flasks are shaken for about 24 hours at about 28°-30° C. and then the pre-cultures (one liter) are used to inoculate jar fermentors, each containing 10 liters of the following nutrient medium:
  • the fermentation batches are incubated aerobically under stirring at 28°-30° C.
  • the antibiotic activity is assayed microbiologically by the standard agar diffusion method using Staphylococcus aureus as the test organism. The maximum activity is reached after 72-96 hours of fermentation.
  • the antibiotics present both in the filtered medium and in the mycelial cake can be extracted with organic solvents by conventional procedures.
  • the filtered medium is adjusted at pH 3.5 by the addition of 8% HCl and then extracted twice with 30% butanol.
  • the organic extracts are concentrated under vacuum at 45° C. to 1/10 of their original volume, washed with a small quantity of water at pH 3.5 and concentrated again to a small volume.
  • the concentrated solution is allowed to stand at low temperature for 10-15 hours until a precipitate forms which is recovered by filtration.
  • the filtered solution is poured in a large amount of light petroleum and the crude precipitate obtained recovered by filtration.
  • the mycelial cake is washed with water at pH 3.5, dried under vacuum and extracted with a 1 to 4 mixture of water to acetone.
  • the acetonic extract is concentrated under vacuum at 40°-45° C.
  • the aqueous residue is adjusted to pH 3.5 and extracted three times with butanol.
  • the collected butanolic extracts are washed with a small quantity of water at pH 3.5 and concentrated under vacuum to 1/20 of their original volume.
  • the concentrated solution is allowed to stand at 4° C. for 10-12 hours.
  • a crude precipitate is obtained which is collected by filtration.
  • the filtered solution is poured in a large amount of light petroleum to give a further precipitate.
  • Antibiotic 8327 factors B and C are separated from each other by employing counter current distribution techniques and isolated as individual antibiotic compounds.
  • a solvent system useful for the separation is a mixture of phosphate buffer M/15 pH 7,0-n-butanol-hexane 1:1:0.05.
  • Teichomycin A 1 , teichomycin A 2 and teichomycin A 3 are separated from each other by column chromatography on Sephadex LH-20, which is a hydroxypropyl derivation of a cross-linked polydextran gel with an exclusion limit at about molecular weight 4,000 and a dry bead diameter of between 25 and 100 microns, using a mixture of n-propanol:ethyl acetate:NH 4 OH 0.2 N 10:7:7 as eluent.
  • the separate antibiotic fractions containing, individually, teichomycin A 1 , teichomycin A 2 and teichomycin A 3 are each concentrated to a very small volume, diluted with methanol and poured in a large volume of acetone. Teichomycin A 1 , teichomycin A 2 and teichomycin A 3 will each precipitate as a whitist amorphous powder.
  • the different chromatographic patterns of the five antibiotics, i.e., antibiotic 8327 factor B and factor C, teichomycin A 1 , teichomycin A 2 and teichomycin A 3 in the various eluting systems are reported in Table IV.
  • the chromatography was on Whatman Paper No. 1, a cotton fibre cellulose filter paper with the following characteristics: weight 85-95 g/m 2 ; thickness 0.16 mm; ash content 0.06-0.07%.
  • 8327 Factor B and 8327 factor C did not show any in vivo activity up to 80 mg/kg. s.c.
  • Teichomycins A 1 , A 2 and A 3 are also active against bacteria which are resistant to widely-used antibiotics such as penicillin, tetracyclin, streptomycin, bacitracin, cephalosporin, rifampicin, streptomycin, neomycin and chloramphenicol.
  • the present invention provides a therapeutic composition
  • a novel antibiotic of the invention together with a pharmaceutically-acceptable carrier.
  • the new antibiotic substances may be useful for different purposes such as controlling infection diseases in animals, disinfection of objects and instruments, growth promoting agents in animals and many other uses which involve suppression of pathogenic bacteria.
  • novel antibiotics of the present invention or compositions containing the same can be applied to bacterial pests or their habitats in microbiocidal amounts to obtain excellent control and kill of many organisms.
  • the novel antibiotics and mixtures thereof with usual additives are equally effective against all such organisms at the same concentration.
  • the novel antibiotics can be employed in an unmodified form or dispersed on a finely-divided solid and employed as a dust. Such mixtures can also be dispersed in water with the aid of a surface-active agent and the resulting emulsion employed as a spray.
  • the novel antibiotics can be employed as the active constituents in solvent solutions, oil-in-water or water-in-oil emulsions.
  • the augmented compositions are adapted to be formulated as concentrates and subsequently diluted with additional liquid or solid adjuvants to produce the ultimate treating compositions. Good results are obtained when employing compositions containing antimicrobial concentrations containing from about 0.5 to about 500 parts by weight of one or more of the novel antibiotics per million parts of such compositions.
  • Teichomycin A 2 obtained according to the procedures as described herein, is an amorphous powder which after further purification by treatment with a cross-linked sulfonated divinylbenzene styrene copolymer cation exchange resin (Dowex 50) in an aqueous solution to pH 4 shows the following chemico-physical properties:
  • I.R. absorption spectrum The complete picture of the spectrum in nujol mull is given in FIG. 2. The most important absorption bands occur at the following frequencies (cm -1 ): 3300 (broad), ⁇ 2900 (nujol), 1720 (shoulder), 1660, 1600 (shoulder), ⁇ 1500, 1455 (nujol), 1375 (nujol), 1235, 1190-930, 850, 720 (broad).
  • the I.R. spectrum was recorded with a Perkin Elmer 157 apparatus.
  • Solubility soluble in aqueous solution at pH 7.0, aqueous sodium bicarbonate, diluted aqueous solutions of alkali hydroxides, methanol-water mixtures; partially soluble in methanol and ethanol; insoluble in diluted mineral acids and in non-polar organic solvents;
  • DMSO dimethylsulfoxide
  • Teichomycin A 1 obtained according to the procedures herein, is further purified by column chromatography on silica gel-celite (1:1 v/v) using a mixture of n-butanol:acetic acid:water (8:2:2) as eluent. It is an amorphous powder with the following chemico-physical properties:
  • I.R. absorption spectrum The complete picture of the spectrum in nujol mull is given in FIG. 3.
  • the mose important absorption bands occur at the following frequencies (cm -1 ): 3350 (broad), 2930-2850 (nujol), 2750-2000, 1720 (shoulder), 1670 (broad), 1620 (shoulder), 1560 (broad), 1460 and 1370 (nujol), 1340 (shoulder) 1260, 1240, 1155 (shoulder), 1120 (shoulder), 1040 (very broad), 970 (broad), 950 (shoulder), 900 (broad) 865, 805, 720.
  • the I.R. spectrum was recorded with a Perkin Elmer 517 apparatus.
  • Solubility soluble in aqueous solution at pH 7.0, aqueous sodium bicarbonate, diluted aqueous solutions of alkali hydroxides, dimethylformamide, dimethylsulfoxide; partially soluble in methanol and ethanol; insoluble in diluted mineral acids and in non-polar organic solvents;
  • Molecular weight Determinations of molecular weight by chromatography through Sephadex G 75, a cross-linked polydextran gel with a range of fractionation, expressed in molecular weight, between 3,000 and 70,000 and a dry bead diameter of between 40 and 120 microns, show the following values: 20,000 in phosphate buffer pH 7.38, 30,000 in citrate buffer pH 4.4.

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US06/030,492 1975-03-05 1979-04-16 Antibiotic substances Expired - Lifetime US4239751A (en)

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MX9203132A MX9203132A (es) 1975-03-05 1992-06-23 Substancias antibioticas.

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GB9057/75A GB1496386A (en) 1975-03-05 1975-03-05 Antibiotics
GB9057/75 1975-03-05

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Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4375513A (en) * 1980-12-18 1983-03-01 Eli Lilly And Company Biologically pure culture of Actinoplanes missouriensis
EP0091649A1 (en) * 1982-04-08 1983-10-19 The Dow Chemical Company Method for increasing the efficiency of rumen fermentation of ruminant animals
EP0093271A1 (en) * 1982-04-08 1983-11-09 The Dow Chemical Company Growth promotion of monogastric animals
US4427656A (en) 1980-08-16 1984-01-24 Gruppo Lepetit S.P.A. Antibiotic A/16686 factor A2, the process for the preparation thereof and the co-produced antibiotic A/16686 factors A1 and A3
EP0137506A2 (en) * 1983-10-11 1985-04-17 The Dow Chemical Company Extraction of teichmonycin a2 from whole culture fermentation broth
US4534969A (en) * 1983-09-19 1985-08-13 The Dow Chemical Company Method for improving lactation in ruminant animals
US4537770A (en) * 1982-03-24 1985-08-27 Eli Lilly And Company A41030 antibiotics
US4542018A (en) * 1982-06-08 1985-09-17 Gruppo Lepetit S.P.A. Teichomycin A2 pure single factors 1, 2, 3, 4 and 5 and method for their production
JPS60243091A (ja) * 1983-12-16 1985-12-03 グルポ・レペチツト・エス・ピ−・エイ 抗生物質ｌ１７３９２及びその塩の化学的製造方法
US4559323A (en) * 1982-03-24 1985-12-17 Eli Lilly And Company A41030 Antibiotics
US4578383A (en) * 1982-12-07 1986-03-25 Warner-Lambert Company CL 1565 antibiotic compounds
US4604239A (en) * 1982-03-24 1986-08-05 Eli Lilly And Company Antibiotics
US4613503A (en) * 1984-10-11 1986-09-23 The Dow Chemical Company Antibiotic A26201-1 and antibiotic A26201-2 produced by a novel strain of actinoplanes
EP0204179A1 (en) * 1985-05-21 1986-12-10 GRUPPO LEPETIT S.p.A. Method for selectively increasing the ratio of single major components of teicoplanin A2 complex
US4645827A (en) * 1983-03-22 1987-02-24 Gruppo Lepetit S.P.A. Glycopeptide antibiotic L 17054
JPS6261998A (ja) * 1985-09-12 1987-03-18 グルポ・レペチツト・エス・ピ−・エイ アミド類およびテイコプラニン化合物
US4713331A (en) * 1982-03-24 1987-12-15 Eli Lilly And Company Microbial production of A41030 antibiotics
US4789661A (en) * 1985-11-28 1988-12-06 Gruppo Lepetit S.P.A. De-(acetylglucosaminyl)-di(dehydro)-deoxy teicoplanin derivatives
US4845194A (en) * 1987-02-27 1989-07-04 Eli Lilly And Company Glycopeptide recovery process
US4859599A (en) * 1984-10-11 1989-08-22 The Dow Chemical Company Antibiotic A26201-1 and antibiotic A26201-2 produced by a novel strain of actinoplanes
US4994555A (en) * 1986-04-11 1991-02-19 Gruppo Lepetit S.P.A. Process for recovery of glycopeptidic antibiotics
US5064811A (en) * 1987-07-03 1991-11-12 Gruppo Lepetit S.P.A. De-mannosyl teicoplanin derivatives
US5085990A (en) * 1987-09-07 1992-02-04 Gruppo Lepetit S.P.A. Teicoplanin-like derivatives
US5164484A (en) * 1985-11-28 1992-11-17 Gruppo Lepetit S.P.A. De-(acetylglucosaminyl-di(dehydro)-deoxy teicoplanin derivatives
US5185320A (en) * 1989-04-03 1993-02-09 Gruppo Lepetit S.P.A. O56 -alkyl derivatives of aglycone and pseudo aglycones of teicoplanin
US5198418A (en) * 1987-03-02 1993-03-30 Gruppo Lepetit S.P.A. Substituted alkylamides of teicoplanin compounds
US5486465A (en) * 1990-10-01 1996-01-23 Gruppo Lepetit S.P.A. Teicoplanin recovery process
US5500410A (en) * 1989-03-29 1996-03-19 Gruppo Lepetit S.P.A. Substituted alkylamide derivatives of teicoplanin
US5567676A (en) * 1986-10-10 1996-10-22 Gruppo Lepetit S.P.A Glycopeptide antibiotics
US5594102A (en) * 1988-12-27 1997-01-14 Gruppo Lepetit S.P.A Chemical process for preparing antibiotic L 17932 (deglucoteicoplanin) and its salt
US5606036A (en) * 1991-03-27 1997-02-25 Gruppo Lepetit Spa Antibiotic A 40926 ester derivatives
US5648456A (en) * 1989-07-18 1997-07-15 Gruppo Lepetit S.P.A. Pentapeptide antibiotics
US5869449A (en) * 1990-12-05 1999-02-09 Gruppo Lepetit S.P.A. 38-decarboxy-38-hydroxymethyl derivatives of teiocoplanin antibiotics and a process for preparing them
US6218505B1 (en) 1996-04-23 2001-04-17 Biosearch Italia S.P.A. Chemical process for preparing amide derivatives of antibiotic A 40926
US20040024177A1 (en) * 2002-07-19 2004-02-05 Ckd Bio Corp. Method for purifying teicoplanin A2
US20040142883A1 (en) * 2002-11-18 2004-07-22 Marco Cavaleri Methods of administering dalbavancin for treatment of bacterial infections
US20050004051A1 (en) * 2002-11-18 2005-01-06 Vicuron Pharmaceuticals, Inc. Methods for treatment of bacterial infections in impaired renal patients
EP1516626A1 (en) * 2003-09-17 2005-03-23 Alpharma APS A Teicoplanin composition with improved antibiotic activity
KR100515186B1 (ko) * 2002-04-23 2005-09-16 주식회사 바이오앤진 테이코플라닌 고생산 변이주 에티노플레네스 테이코마이세티쿠스를 이용한 테이코플라닌의 발효 제조방법
US20050245481A1 (en) * 2004-04-16 2005-11-03 Dong Kook Pharmaceutical Co., Ltd. Method of producing teicoplanin
US20060074014A1 (en) * 2002-11-18 2006-04-06 Vicuron Pharmaceuticals Inc. Dalbavancin compositions for treatment of bacterial infections
EP1671640A1 (en) * 2004-12-17 2006-06-21 Biongene Co. Ltd. Mutant strain of Actinoplanes teichomyceticus for the production of teicoplanin
US20060134757A1 (en) * 2004-12-17 2006-06-22 Soo-Ryun Cheong Microorganism and the process for the production of teicoplanin
EP2592089A1 (en) 2011-11-11 2013-05-15 LEK Pharmaceuticals d.d. Process of purification of teicoplanin
EP2592090A1 (en) 2011-11-11 2013-05-15 LEK Pharmaceuticals d.d. Process of purification of teicoplanin

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AT382380B (de) * 1982-06-08 1987-02-25 Lepetit Spa Verfahren zur auftrennung des teichomycin a2-komplexes

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DE2615534C3 (de) * 1976-04-09 1978-10-05 Jenaer Glaswerk Schott & Gen., 6500 Mainz Für die Nachrichtenübertragung geeignete Lichtleitfaser mit Gradientenprofil aus Mehrkomponentengläsern mit angepaßtem Ausdehnungskoeffizienten zwischen Glaskern und Glasmantel sowie Verfahren zu ihrer Herstellung

Patent Citations (1)

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US3824305A (en) * 1973-01-22 1974-07-16 Lilly Co Eli Antibiotic a-287 and process for production thereof

Cited By (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4427656A (en) 1980-08-16 1984-01-24 Gruppo Lepetit S.P.A. Antibiotic A/16686 factor A2, the process for the preparation thereof and the co-produced antibiotic A/16686 factors A1 and A3
US4375513A (en) * 1980-12-18 1983-03-01 Eli Lilly And Company Biologically pure culture of Actinoplanes missouriensis
US4537770A (en) * 1982-03-24 1985-08-27 Eli Lilly And Company A41030 antibiotics
US4713331A (en) * 1982-03-24 1987-12-15 Eli Lilly And Company Microbial production of A41030 antibiotics
US4559323A (en) * 1982-03-24 1985-12-17 Eli Lilly And Company A41030 Antibiotics
US4604239A (en) * 1982-03-24 1986-08-05 Eli Lilly And Company Antibiotics
EP0093271A1 (en) * 1982-04-08 1983-11-09 The Dow Chemical Company Growth promotion of monogastric animals
EP0091649A1 (en) * 1982-04-08 1983-10-19 The Dow Chemical Company Method for increasing the efficiency of rumen fermentation of ruminant animals
US4542018A (en) * 1982-06-08 1985-09-17 Gruppo Lepetit S.P.A. Teichomycin A2 pure single factors 1, 2, 3, 4 and 5 and method for their production
US4578383A (en) * 1982-12-07 1986-03-25 Warner-Lambert Company CL 1565 antibiotic compounds
US4645827A (en) * 1983-03-22 1987-02-24 Gruppo Lepetit S.P.A. Glycopeptide antibiotic L 17054
US4650855A (en) * 1983-03-22 1987-03-17 Gruppo Lepetit S.P.A. Glycopeptide antibiotic L 17046
US4534969A (en) * 1983-09-19 1985-08-13 The Dow Chemical Company Method for improving lactation in ruminant animals
US4696817A (en) * 1983-10-11 1987-09-29 The Dow Chemical Company Extraction of teichomycin A2 from whole culture fermentation broth
EP0137506A2 (en) * 1983-10-11 1985-04-17 The Dow Chemical Company Extraction of teichmonycin a2 from whole culture fermentation broth
EP0137506A3 (en) * 1983-10-11 1987-06-16 The Dow Chemical Company Extraction of teichmonycin a2 from whole culture fermentation broth
JPH0653746B2 (ja) * 1983-12-16 1994-07-20 グルポ・レペチツト・エス・ピ−・エイ 抗生物質ｌ１７３９２及びその塩の化学的製造方法
JPS60243091A (ja) * 1983-12-16 1985-12-03 グルポ・レペチツト・エス・ピ−・エイ 抗生物質ｌ１７３９２及びその塩の化学的製造方法
US4859599A (en) * 1984-10-11 1989-08-22 The Dow Chemical Company Antibiotic A26201-1 and antibiotic A26201-2 produced by a novel strain of actinoplanes
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LU88311I2 (fr) 1994-05-04
NO145342C (no) 1982-03-10
DK92776A (sv) 1976-09-06
IL49094A (en) 1979-05-31
PH18612A (en) 1985-08-21
FI54145B (fi) 1978-06-30
IL49094A0 (en) 1976-04-30
AU1152176A (en) 1977-09-08
NO145342B (no) 1981-11-23
JPS5629880B2 (sv) 1981-07-10
MX3839E (es) 1981-08-11
PT64865B (en) 1977-07-20
FI54145C (fi) 1978-10-10
DK141022B (da) 1979-12-24
NO760725L (sv) 1976-09-07
NZ180194A (en) 1978-06-02
BE839259A (fr) 1976-09-06
RO68837A (ro) 1980-09-26
IN142259B (sv) 1977-06-18
SE432782B (sv) 1984-04-16
HU171790B (hu) 1978-03-28
YU40134B (en) 1985-08-31
AR207809A1 (es) 1976-10-29
IE44090B1 (en) 1981-08-12
NL166062C (nl) 1981-06-15
IE44090L (en) 1976-09-05
GB1496386A (en) 1977-12-30
ES445799A1 (es) 1977-09-16
NL7602258A (nl) 1976-09-07
SU579902A3 (ru) 1977-11-05
DE2608216A1 (de) 1976-09-23
SE7602864L (sv) 1976-09-06
NL930028I2 (nl) 1993-09-16
NL930028I1 (nl) 1993-06-01
LU74476A1 (sv) 1976-09-01
DK141022C (sv) 1980-06-09
ZA761119B (en) 1977-04-27
DD124606A5 (sv) 1977-03-02
PT64865A (en) 1976-04-01
NL166062B (nl) 1981-01-15
AT342766B (de) 1978-04-25
GR64305B (en) 1980-03-03
CS198184B2 (en) 1980-05-30
FI760562A (sv) 1976-09-06
ATA159776A (de) 1977-08-15
HK46182A (en) 1982-11-12
PL98593B1 (pl) 1978-05-31
JPS5830037B2 (ja) 1983-06-27
JPS55102598A (en) 1980-08-05
DE2608216C2 (de) 1984-12-20
FR2302748B1 (sv) 1978-11-17
AU501202B2 (en) 1979-06-14
CH611931A5 (sv) 1979-06-29
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YU57176A (en) 1982-10-31
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FR2302748A1 (fr) 1976-10-01

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